It's really hard for me to say, since I've been collecting on and off since i was like six years old. I think the first one I ever actually baught with my own money was G2 Bumblebee, which I still have. But at that age I really only baught a few and they were for fun. I started buying TFs again when Beast Wars came out, and the first ones I got was a two-pack of Armordillo and that Iguana guy. I baught a lot of BW figures, but again, they were for play. It was only last summer that I re-discovered TFs and how awesome they are. I was working a lame office job and needed some entertainment, so I picked up the mini-version of Cybertron Jetfire. Then I found alternators. I was at Zellers, and they had Sideswipe (the Viper has ALWAYS been my favorite car). Problem is, they were asking 39.99 for him. He was in an opened box, totally loose, with no instructions. And they refused to give me a discount. I eventually said "fuck this" and walked out with him in my pocket. The only thing I've ever stolen, and I don't feel the least bit bad about it. I baught a few more here and there, but I don't think I decided to actually collect until I picked up Classics Jetfire. I just sorta said to myself..."hey, I have the money, so why not collect?"

So I guess in a way, Cybertron Jetfire is what got me started, but my first official collection purchase was Classics Jetfire. Hell of a way to start  

 

omg youre a criminal!

reissue lambor started me back on TFs as an adult but RID magnus (the tfu repaint) really opened the doors for to modern TFs.

that was like in 2005 i think after AOTC came out and im close to 300 bots right now.

 

Alternator Grimlock....and here i am a almost a year and 500 TFS later

 

Well, I still have all my childhood G1 Transformers and my 1st one as a kid was skywarp. As an adult, the 1st thing I bought was the D-16s Megatron reissue, the 1st megatron reissue, then it was all down hill from there.

 

G1 Starscream when I was 2. still have him somewhere. well, some of him. I was a fan clear up until Beast Machines killed transformers for me. then I got RID Optimus Prime on a whim after seeing the show and thinking he had a cool transformation scheme.

So those are the two transformers that started each phase of my collecting.

 

The one that started my passion is Skywarp...he was my first TF as a kid.

The one(s) that got me back into collecting full time again? The first wave of the Cybertron line. For me, those were the first TFs that were actually cool to me. Armada and Energon didn't do that.

 

My first TF was G1 Prowl...I bought BW Dinobot in 1995 but I hated the idea of beast wars back then (an idiot move). I saw a couple BW shows, softened a little on the concept and got TM2 Cheetor and Dinobot. Then I got back into collecting full time with the RiD car Brothers. Got Prowl and X-Brawn, soon after found Sideburn, then just went crazy with the rest 

So I just realized I got a Prowl toy as a kid, then a Prowl toy to start off my adult collecting full time...haha never thought of that!

 

As a kid, IIRC it was G1 Gears.

As a more serious adult collector, it was Alt Tracks. But I did a few peeks into the lines between G1 and Alts, including RID Ops and Scourge. Never did get into any Beast Wars stuff or Armada/Energon.

 

Micron Legend Jetfire. Oh how amazed I was to see the toy "just like in the cartoon!!"  

KA...your sig makes me cry.

 

Bots, G1 Smokescreen and Jetfire in 1985.  

 

RID Prowl and Skybyte started my collecting habit  

 

car robots convoy. I thought the fire truck was cool and the nostalgia factor was high. 6 years and 800+ tfs later I am hooked...  ....  

 

Micronauts Baron Karza was the first toy I re-bought from my youth   That was in 1981...my first TF was Megatron...followerd by all of the first wave of 1985 robots (I spent an entire paycheck   )

 

Starting back up again it was BW Optimal Optimus 10 years ago.

 

G2 Rapido and Skram at the age of 2....of course I was 2, so their real names were "Bob" and "Squirt". Good times...good times
DN

 

I got a few G1 toys when I was a kid, and some BW figures too that I sort of collected. But my serious adult collecting began with Energon Starscream.

 

Well, for my oddity collation it would have to be the little G1 Optimus Prime radio I won on ebay a few years ago. I LOVED how unique it was and began to start looking for more radios and before I knew it I have entire room just full of TF merchandising items.  

 

My first Transformer was a wedding present back in 1987, Scattershot. I then went out and bought the other four Technobots, opened them and put them on display. After realizing my error, I went out and bought all five and left them sealed. That was 20 years and well over 1500 Transformers ago. 

 

I hate to admit it, but it was Brawn. I had never heard of Transformers when they had first come out. In the fall of 1984, my little brother brought Brawn home from school. I saw him playing with it and was fascinated that it was a vehicle and robot all in one toy. I never really collected anything, so I figured I would start collecting Transformers. I paid for them at first with my paper routes and then later with the money I made as a caddy. I stopped post-movie in the middle of the fourth toy series and really regret that. I saw many Fort Maxes on the shelf. I passed, since I no longer collect them. I started collecting again in late 2000 with the Takara reissues. I still have every original Transformer from my childhood. In the beginning, yeah, it was Brawn for me.  

 

Probably would have to say my JBW C-1 Convoy. I bought him, oh, probably almost 10 years ago for $30 shipped from the old camecave.com. He was my first import, and the one tha really started my collection.

Of course, as a kid i had a lot of TFs and other toys... but I wasn't a "collector" then.